Dooling's first novel, Critical Care (1992), was made into a 1997 movie of the same title, directed by Sidney Lumet and starring James Spader and Kyra Sedgwick. His next three novels—White Man's Grave (1994), Brain Storm (1998), and Bet Your Life (2002)—were all New York Times Notable Books. In conjunction with Kingdom Hospital, he also wrote The Journals of Eleanor Druse (2004), writing as Eleanor Druse, a character in the miniseries. Dooling's short story "Bush Pigs" was read as part of Selected Shorts, a program produced by Symphony Space in New York and aired on NPR. The performance was later included on the CD Getting There from Here, a compilation of listeners' favorites from the program.[1]

His nonfiction book Blue Streak: Swearing, Free Speech, and Sexual Harassment (1996) is an examination of the social and legal implications of profane speech. In Rapture for the Geeks: When AI Outsmarts IQ (2008) he explores the implications of machine intelligence overtaking human intelligence. He has also written op-ed pieces for The New York Times, The Wall Street Journal, and The National Law Journal.